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We’re days away from the official opening of the NHL free-agency market. On Sunday at noon, the league’s UFAs will be free to start signing with any team they’d like.

Well, they won’t be free. Many of them will be quite expensive. In some cases, ridiculously expensive. And most of them won’t end up being worth it.

That’s kind of how it goes at this time of year, as NHL GMs compete to see who can make the biggest UFA mistake. The occasional big signing works out, and some come and go with only minor pangs of regret. But others will be disasters that will leave us wondering what anyone was thinking.

The days ahead may feel like chaos. But the sort of deals we see actually fall into some predictable categories. In fact, with the benefit of a little hindsight, we can evaluate most UFA signings by asking three questions.

Was the player a good fit? In other words, did it make sense for the team to sign this player in the first place, given their roster and their needs in other areas? Was he even any good?

Did the deal carry a reasonable annual cap hit? Self-explanatory, and probably the first question we wonder about when we hear about a new signing.

Did the team commit to a reasonable term? How many years did a team have to cough up to get a deal done? This tends to take a back seat to cap hit in most of the immediate evaluations, although it probably shouldn’t.

Combine those three categories and you’re left with what we could call the Fit-Hit-Term scale. By answering yes or no to each question, we can figure out which of eight different categories a deal might fall into. And we can look back through the cap era to find the UFA signings that best represent each one.

We’ll start with the best possible kind of signing. These are the deals where everything makes sense. The player is a star who fills a need. The cap hit may sting a little but isn’t unreasonable. And the length of the deal means a team won’t spend most of it paying star money to a player who’s well past his prime.

Here’s the bad news: Man, there aren’t many significant signings that fall into this category.

In fact, you could make the case that the two best UFA signings of the cap era both came well over a decade ago. Scott Niedermayer’s four-year deal with the Ducks back in 2005 worked out beautifully, as Anaheim nabbed the reigning Norris winner and were celebrating a Stanley Cup within two years. That was followed by Zdeno Chara signing a five-year deal with Boston in 2006 that carried a $7.5-million cap hit through his early 30s. By the end of that deal, he’d won a Norris and a Stanley Cup.

Both deals made sense at the time, and look even better in hindsight. They also both came before teams decided to start agreeing to contracts that carried massive term. That trend started around 2009, give or take a year, and since then it’s been hard to find a major UFA deal that checks all three boxes.

You could probably pick out a few other candidates from recent years, depending on how willing you are to stretch the concept of a “major” deal – if you want to count guys like Anton Stralman in Tampa or Alexander Radulov in Montreal, your list gets a bit longer. But if you’re looking at the big names, it’s slim pickings. The best a GM can really hope for these days is to go two-for-three, which will make up our next few categories.

Category #2: Good fit, good hit, bad term (aka “The Hossa”)

You still see these deals crop up from time to time. But the golden era for this sort of signing came in the years leading up to the 2013 lockout, as teams (and agents) figured out that going long on term could result in a reduced cap hit. Back then, going long meant really long, often well into the double-digits in terms of years. When those deals didn’t work out, they were disasters, because you were locked in forever. When they did work, you got The Hossa.

Back in 2010, Marian Hossa was on the open market for the second straight year. The previous summer, he’d signed a one-year deal to chase a Cup with the Wings, which didn’t really work out. This time, the 31-year-old was looking to sign a deal that would be his last in the NHL. And that’s what he got, as the Blackhawks gave him an eye-popping 12 years in exchange for a discount cap hit of just $5.275 million. Hossa was a perfect fit in Chicago, and helped them win three of the next six Cups. And due to a rare skin condition, his playing days ended well before the contract turned into a cap albatross.

The NHL changed the rules around long-term deals in 2013, so Hossa-like bargains are harder to find these days. But every year, teams still convince themselves that they can add the final piece of a championship puzzle at a reasonable cost by going as long as possible on term. Hey, if it doesn’t work out, it will probably be the next GM’s problem, right?

A relative rarity, these deals carry a pricey cap hit but a reasonable term. Back in 2014, the Blues managed to land one of the top centres on the market in 28-year-old Paul Stastny. He didn’t come cheap, with a cap hit of $7 million that seemed pricey for a guy who hadn’t topped 60 points since 2010. But the deal was only for four years, meaning the Blues wouldn’t be on the hook past his early 30s. It felt like a reasonable gamble, and it mostly paid off – Stastny was solid for three seasons, and then the Blues flipped him at the deadline for a first-round pick during his walk year.

These days, Stastny is 32 and ready to hit the open market again. It will be interesting to see what kind of deal he’s willing to take this time around.

In theory, these contracts are better than the inverse low-hit/high-term arrangements, since the shorter length keeps the risk of the deal turning truly disastrous to a minimum. But over the years, teams have made it clear that they’d rather kick the can down the road in exchange for some cap savings up front. It rarely works out.

Category #4: Bad fit, good hit, good term (aka “The Shattenkirk”)

Generally speaking, you don’t know these deals when you see them. Instead, you’re left thinking a team got a steal, locking in a good player at a decent price and term. But then the new addition never quite clicks, and you start to wonder if it was really worth it.

Kevin Shattenkirk‘s contract with the Rangers last summer fits the bill. He took a hometown discount on a four-year deal to play with the team he grew up watching, and virtually everyone agreed that New York was a big winner. But Shattenkirk was just OK in his debut season on Broadway, and the Rangers wobbled through a shaky first half before deciding to rebuild. Now, you wonder if they’d prefer a do-over, even with only three years left on the deal.

Occasionally you’ll get deals where the fit makes so little sense that they require an additional move down the line. One memorable example from the pre-cap days came in 1998, when the Maple Leafs signed Curtis Joseph to a big deal despite already having an established starter in Felix Potvin. Joseph was fantastic, Potvin was eventually traded, and the signing ended up being one of the best of its era.

Sportsnet Tonight

June 28: Looking ahead to free agency frenzy

June 28 2018

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Category #5: Good fit, bad hit, bad term (aka “The Lucic”)

Sadly, this is probably the most common category. A team decided that it absolutely has to have a certain player, and they pay whatever it takes to make it happen. Inevitably, “whatever it takes” ends up being way too much for way too long.

We’re naming this one after Milan Lucic’s 2016 deal with the Oilers, although you could go with any number of other candidates. Scott Gomez comes to mind. So does Chris Drury, or Danny Briere, or Brad Richards, or Nathan Horton, or Zach Parise, or Andrew Ladd, or David Backes, or a dozen more. NHL GMs love signing deals in this category more than their own children.

In Lucic’s case, Peter Chiarelli’s understandable desire to reunite with the power forward who helped him win a Cup in Boston led to a contract that everyone knew would quickly become a disaster. Sure, the idea of Lucic playing the dual role of Connor McDavid’s winger and bodyguard made sense on some level. Just not for seven years, or for a buyout-proof $6 million a season. Not surprisingly, the Oilers are reportedly trying to get out of the deal just two seasons later, and Chiarelli’s reputation in Edmonton has taken a major hit.

Category #6: Bad fit, good hit, bad term (aka “The Leino”)

You don’t see many of these deals, which sounds like a positive until you realize that it’s because most GMs can’t seem to get a decent cap hit on any UFA deal, even the ones that already disasters for other reasons. One recent example would probably be Matt Beleskey with the Bruins, but you have to go back a bit further to find the archetype.

When Ville Leino hit the market in 2011, he was 27 and coming off a career-best 53-point season. He was also one season removed from a 21-point playoff run. All things considered, a $4.5-million cap hit for a youngish winger with some sandpaper who could slot into a top six wasn’t bad. It certainly wasn’t great, bit it wasn’t bad.

What was bad was the term; the Sabres gave Leino six years, which meant they were screwed if his big season turned out to be a fluke. Spoiler alert: It was. He was a major bust in Buffalo, scoring just 10 goals in three seasons, and was bought out in 2014. He hasn’t played in the league since.

(This was actually one of two Category #6 deals that the Sabres signed in 2011, with a 10-year deal for Christian Ehrhoff also eventually ending with a buyout. New owner Terry Pegula wanted to make a splash, and he did. It just wasn’t the kind he wanted.)

This is another category that’s relatively rare. It also tends to be a rollercoaster for fans, since you hear your team is interesting in a guy (oh no) and then hear about the cap hit (OH NO) before realizing the deal is only for a year or two.

Alexander Semin‘s 2012 deal with the Hurricanes may be the best example. After peaking with an 84-point season in 2009–10, he’d plunged down to consecutive 54-point campaigns amidst rumours of a poor attitude and work ethic. That made him a decidedly risky target for any team. But the Hurricanes rolled the dice, and did so with a jaw-dropping $7-million cap hit. But the deal was just for one year, so even if Semin was a total bust, the contract wouldn’t be a disaster.

Well, unless he was reasonably productive for one lockout-shortened season, and then the Hurricanes threw a five-year extension at him that carried that same $7-million hit. Whoops.

Category #8: Bad fit, bad hit, bad term (aka “The Clarkson”)

This is it. The mother of all bad contracts. The one that doesn’t make any sense on any level. The player isn’t good, or at least isn’t a good fit for this team at this time. The cap hit is way too high. And the term is way too long. An NHL contract can’t get any worse than this.

There was no shortage of examples for this category.

We’ll go with the Leafs’ 2013 signing of David Clarkson to a seven-year deal that carried a $5.25-million cap hit that was essentially impossible to buy out. It was a ridiculous overpay for a player who was already a year removed from his only 20+-goal season. And contrary to the revisionist history you occasionally hear floated these days, criticism of the deal didn’t only pop up in hindsight. Most of us who were paying attention hated it at the time. “The money is unnerving, but the term is absolutely frightening”, said Sports Illustrated. “This has regret written all over it,” predicted Yahoo. The Leafs were free agency’s biggest losers – “by a lot,” screamed a Sporting News headline.

If anything, the deal ended up being worse than anyone thought. At the time, Nonis infamously told reporters that he was “not worried about (years) six or seven right now,” explaining that “I’m worried about one. And year one, I know we’re going to have a very good player.” He was wrong. Clarkson was a bust from the start, even before injuries effectively ended his career. Only a technicality on Nathan Horton’s contract with the Blue Jackets allowed the Leafs to wriggle out of Clarkson’s cap hit, albeit at a cost of roughly $25 million in real dollars.

The Clarkson deal was awful from day one. But it’s far from alone among recent UFA deals. Loui Eriksson‘s contract with the Canucks fits here, too. So would signings like Ryan Clowe in New Jersey, or Dave Bolland in Florida. Going back a bit further, there’s Wade Redden with the Rangers. Ilya Bryzgalov would probably be the king of this category, although his deal was technically an extension after the Flyers traded for his rights.

You can probably think of a few more that your favourite team has signed. And if not, don’t worry — there’s a good chance they’ll find one over the coming days. NHL GMs love them some Category #8.

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